S-Adenosylcoenzyme M, (+)-S-Methyl Adenosyl coenzyme M: Preparation and Role in Methane Biosynthesis
Cullen, W.R., David Dolphin, Hoffman, D., and Trip, E.
Can. J. Chem.
5'-S-(2-Sulfoethyl)-5'-deoxy-5'-thioadenosine (S-adenosylcoenzyme M) (I) was prepared from adenosine by reacting its 2',3'-isopropylidine tosylate with the disodium salt of coenzyme M (NaSCH2CH2SO3Na) followed by removal of the protecting group. Methylation of I to give methylsulfonium (±) S-adenosylcoenzyme M (II) was achieved with CH3I in HOAc. Neither I nor II stimulated CH4 production from cell free preparations of M. thermoautotrophicum, negating the possibility of a biochemical analogy between II and S-adenosylmethionine.